How Brett Hickey Built a $Billion Firm From Nothing | Leadership & PE Lessons Every CEO Must Hear

Episode Summary:
In this insightful episode, Alex Rawlings is joined by Brett Hickey, the CEO and founder of Star Mountain Capital. Brett shares his unique journey from humble beginnings in Northwestern Canada to leading a multi-billion-dollar asset management firm in the U.S. With deep reflections on leadership, value-based investing, building collaborative ecosystems, and what truly drives sustainable success in private markets, this is a masterclass in private equity thinking.

Brett also discusses the strategic opportunities in the U.S. lower middle market, the implications of aging demographics, his risk-aligned investment strategy, and the power of culture in scaling a firm. If you're looking to understand how to build a high-performing investment organization from the ground up—and what books, frameworks, and philosophies support that—this episode is essential listening.

⏱️ Episode Highlights & Time Stamps:

00:00 – Welcome and Introduction to Brett Hickey
00:41 – Overview of Star Mountain Capital and its focus on U.S. lower-middle market private credit, secondaries, and private equity
01:12 – Key mistake PE firms make: passive asset management vs. active value creation
03:08 – Aging demographics as a key investment opportunity
04:05 – Valuation arbitrage in lower middle market businesses
05:05 – Reflections on a possible downturn: macroeconomic risks and “air pockets”
07:59 – Aging populations and structural economic concerns
09:53 – The importance of cash flow and capital protection
10:21 – Brett’s entrepreneurial journey – from launching his first fund at 26 to building Star Mountain Capital
12:41 – The S-shaped growth curve and persistence through innovation
13:40 – Brett’s data-driven approach to strategy and decision making
15:35 – Why aging demographics and inefficient markets create opportunity
17:08 – Biggest challenge in building the firm: People
19:30 – Aligning team culture and expectations through transparency and shared values
20:57 – Why Star Mountain is 100% employee-owned – benefits and challenges
22:54 – Building trust and long-term alignment through ownership
24:45 – Observations on asset management failures and strategic missteps
25:44 – What is the Collaborative Ecosystem and how it drives results at Star Mountain
27:34 – How peer networks like EO and YPO influenced the firm’s internal culture
28:31 – Leveraging insights between secondaries and direct investments
29:59 – Case studies, adjusted EBITDA, and forensic underwriting
31:18 – Using real business alignment as a differentiator in competitive deal processes
33:13 – Recommended reading: Brett’s top books and content on leadership and execution
33:41 – Never Lead Alone by Keith Ferrazzi
34:37 – Agility by Leo Tilman and General Chuck Jacoby
36:54 – Harvard Business Review and Rob Kaplan’s work on leadership
38:48 – Principles by Ray Dalio and how it influences Brett’s thinking
39:18 – A practical tip: triangulating decisions with deep experts
41:13 – Final reflections on value investing, risk management, and staying grounded
42:09 – How to get in touch with Brett and Star Mountain Capital
42:38 – Wrap-up and takeaways from Alex

🔗 Connect with Alex Rawlings on LinkedIn: https://www.linkedin.com/in/alexrawlings/
🌐 Visit Raw Selection: www.raw-selection.com